Florida Keys Holidays Sizzle with Sparkle and Warmth

FLORIDA KEYS — Sunny, breezy subtropical holidays in the Florida Keys & Key West are filled with warmth and good cheer throughout the 125-mile-long island chain. From Key Largo to Key West, the 2022 holiday season features spirited events such as lighted boat parades, holiday markets, historic inn tours, only-in-the Keys frivolity, sparkling waterfront celebrations and other island festivities.

Select Keys holiday events are outlined below, while additional Florida Keys & Key West events can be found at fla-keys.com/calendar.

Through Dec. 31: Harbor Walk of Lights. Key West. The Harbor Walk of Lights at the Key West Historic Seaport stretches along the harbor past Greene, William and Margaret streets to the Key West Ferry Terminal. Attractions include a 20-foot-tall Fishing Buoy tree, a 16-foot Nautical Christmas tree and a Key West Lobster Trap tree. Visit keywestchristmas.org.

Through Dec. 31: Key West Holiday Fest. Key West. A merry range of celebrations during the island city’s busy holiday season includes lighting of the Harbor Walk of Lights and Holiday Historic Inn Tours. Visit keywestholidayfest.com. 

Dec. 8-23: Old Town Trolley's Holiday Sights & Festive Nights Tours. Key West. The popular green and orange trolleys, festively adorned with holiday lights, showcase Key West's best-decorated neighborhoods, buildings and homes on fun-filled 60-minute excursions. Tours depart each evening from Mallory Square at 6:30, 7, 8 and 8:30 p.m. Visit trolleytours.com/key-west/christmas-holiday-tours or call 855-623-8289 or 305-296-6688.

16-23: Conch Tour Train's Holiday Sights & Festive Nights Tours. Key West. Lively Conch Tour Train tours depart from Key West High School, 2100 Flagler Ave., at 6:30, 7, 8 and 8:30 p.m. Included are holiday lights glasses as keepsake items. The tour takes riders past the island's most elaborately decorated houses, buildings and neighborhoods, with holiday caroling. Visit conchtourtrain.com/key-west-holiday-events.html or call 305-707-5775 or 305-296-6688.

Dec. 16: Holiday Historic Inn Tour. Key West. Old Town Key West is filled with unique historic properties and inns, from 6-8 p.m. this tour offers a chance to glimpse lavish decorations and experience holiday cheer and treats at bed-and-breakfast properties and attractions. Visit keywestholidayfest.com or keystix.com or call 305-296-4959.

Dec. 17: Annual 5K Rudolph Red Nose Run. Key West. This spirited early morning run kicks off at 7 a.m. at Southernmost Beach Café, 1405 Duval St. Visit keywestinns.com or call 305-295-6550.

Dec. 17: Winter Wonderland at Crane Point. Marathon. At Crane Point Hammock Museum & Nature Trails, 5550 Overseas Highway, families can enjoy an evening winter wonderland. Attractions are to include reindeer ponies and Santa Claus, holiday decorations, a chocolate fountain, other seasonal treats and alcoholic drinks for purchase — plus a forecast of snow! Visit cranepoint.net or call 305-743-9100.

Dec. 18: Lighting of the Menorah. Key West. The City of Key West's annual Menorah Lighting ceremony takes place at Bayview Park from 5 to 6 p.m.

Dec. 18, Jan. 1: Artisan Market. Key West. A “shop local” holiday tradition, the open-air bazaar is from 10 a.m. to 2 p.m. at Indigenous Park at Higgs Beach, 100 Atlantic Blvd. Each event is given a theme and all feature Keys artists, authors, chef-made cuisine, craftspeople, performers, live music and adult beverages. Admission is free. Visit facebook.com/KeyWestArtisanMarket or call 305-509-3385.

Dec. 28 and 29: Home Tours “Holiday Style.” Key West. The Old Island Restoration Foundation’s Key West Home Tours are among America’s oldest and longest-running, dating from 1960. This 63rd series features self-guided tours of several Key West homes and gardens, each festively dressed. Three additional tour weekends are scheduled in 2023, with dates set for Jan. 13-14, Feb. 17-18 and March 17-18. Visit oirf.org or call 305-294-9501.

Dec. 30: Glow Pary & Fireworks Show. Key West. The annual Glow Part and Fireworks show takes place from 6 to 10 p.m. at Key West Marriott Beachside. Organizers will give away over two thousand glow items to brighten up your night. DJ Sanaris provides the tunes. Proceeds from food available for purchase supports Take Stock in Children. Fireworks start at 9 p.m. 

Dec. 31: New Year's Eve “Drops” in Key West. Ring in 2023 with a “conch shell drop” at Sloppy Joe's Bar, 201 Duval St.; the 25th anniversary of the descent of a super-sized red high-heel shoe carrying drag queen Sushi at the Bourbon St. Pub/New Orleans House complex, 724 Duval St.; the lowering of a pirate wench at midnight from atop a tall ship’s mast at the Schooner Wharf Bar, 202 William St.; and a huge replica of a Key lime wedge splashing down into a larger-than-life margarita glass, paired with a performance by The Beatle Band, at Ocean Key Resort & Spa, 0 Duval St. Revelers can also witness the “flight” of a uniformed “stewardess” in a section of a replica aircraft and enjoy a ticketed Gatsby-style party at First Flight Island Restaurant & Brewery, 301 Whitehead St., known as the birthplace of Pan American Airways. In addition, there’s a “tuna drop” at the Smokin’ Tuna Saloon, 4 Charles St. Visit sloppyjoes.com, bourbonstpub.com, schoonerwharf.com, facebook.com/SunsetPierKeyWest/, firstflightkw.com and smokintunasaloon.com.